Chemistry 506: Allied Health Chemistry 2. Chapter 15: Amines and Amides. Functional Groups with Single Bonds to Nitrogen
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1 Chemistry 506 Dr. Hunter s Class Chapter 15. Chemistry 506: Allied Health Chemistry 2 1 Chapter 15: Amines and Amides Functional Groups with Single Bonds to Nitrogen Introduction to General, Organic & Biochemistry, 5 th Edition by Bettelheim and March: Chapter 15, Pages Outline Notes by Dr. Allen D. Hunter, YSU Department of Chemistry, Outline 15A SECTION(S) 15.1/2/3 AMINES B SECTION(S) 18.2 AMINO ACIDS HAVING AMINE/HETEROCYCLIC CONTAINING SIDE CHAINS C SECTION(S) 15.4 AMINE BASICITY D SECTION(S) 15.5/6 AMIDES E SECTION(S) 15.7/8 AMIDE REACTIONS F SECTION(S) 18.2 AMINO ACIDS HAVING AMIDE CONTAINING SIDE CHAINS... 17
2 Chemistry 506 Dr. Hunter s Class Chapter A Section(s) 15.1/2/3 Amines 2 Amine Classification Ammonia 1, Primary Amine 2, Secondary Amine
3 Chemistry 506 Dr. Hunter s Class Chapter 15. 3, Tertiary Amine 3 4, Quaternary Ammonium Salts
4 Chemistry 506 Dr. Hunter s Class Chapter 15. IUPAC Nomenclature 4 Named as Alkyl Amines (multiple words) Dimethyl Amine Methyl Ethyl Amine Tetramethyl Ammonium Chloride
5 Chemistry 506 Dr. Hunter s Class Chapter 15. Aromatic Amines 5 Aniline (coal tar) N-methyl-N-ethyl aniline
6 Chemistry 506 Dr. Hunter s Class Chapter 15. Heterocyclic Amines 6 Pyridine (C 5 H 5 N, coal tar) Piperidine (C 5 H 11 N) Pyrimidine (1,3-C 4 H 4 N 2 ) Pyrole (C 4 H 5 N) Pyrrolidine (C 4 H 9 N)
7 Chemistry 506 Dr. Hunter s Class Chapter 15. Properties 7 Relatively high Mp and Bp Polar Hydrogen Bonding Donor Hydrogen Bonding Acceptor Solubility Stench! Putrescine H 2 N-(CH 2 ) 4 -NH 2 Cadaverine H 2 N-(CH 2 ) 5 -NH 2 Hydrogen Bonding H-bonding donors and H-Bonding acceptors
8 Chemistry 506 Dr. Hunter s Class Chapter B Section(s) 18.2 Amino Acids having Amine/Heterocyclic Containing Side Chains Amino Acids (Building Blocks of Proteins) Generic AA = H 2 N-CHR-CO 2 H Lysine (basic) R = CH 2 CH 2 CH 2 CH 2 -NH 2 Tryptophan (neutral polar) Nitrogen is in aromatic bond H 2 C N H Histidine (basic) H 2 C N N H Arginine (basic) CH 2 CH 2 CH 2 NH-C(=NH 2 )-NH 2
9 Chemistry 506 Dr. Hunter s Class Chapter C Section(s) 15.4 Amine Basicity 9 Simple Acid/Base Chemistry All Amines plus acids such as H + (ammonium salts) Neutralization of ammonium salts by bases such as OH -
10 Chemistry 506 Dr. Hunter s Class Chapter Amines plus Alkyl Halides Generic (Nucleophilic Attack and Deprotonation) NH 3 plus Alkyl Halides NH 2 R plus Alkyl Halides NHR 2 plus Alkyl Halides
11 Chemistry 506 Dr. Hunter s Class Chapter NR 3 plus Alkyl Halides no deprotonation possible
12 Chemistry 506 Dr. Hunter s Class Chapter D Section(s) 15.5/6 Amides Generic Structures Properties Mp and Bp Polarization of Bonds Hydrogen Bonding Lone Pairs Neither Acidic or Basic
13 Chemistry 506 Dr. Hunter s Class Chapter IUPAC Nomenclature anamide examples Butanamide Benzamide N,N-dimethylbutanamide
14 Chemistry 506 Dr. Hunter s Class Chapter E Section(s) 15.7/8 Amide Reactions Direct Synthesis from Carboxylic Acids and Amines Acid/Base reaction Thermolysis Synthesis from Acid Chlorides Synthesis from Anhydrides
15 Chemistry 506 Dr. Hunter s Class Chapter Nylon 66 Synthesis by Direct Reaction of Carboxylic Acids and Amines Synthesis from Acid Chlorides and Amines Related to Protein Backbones Polyamides with Side Chains
16 Chemistry 506 Dr. Hunter s Class Chapter Hydrolysis of Amides Acidic Hydrolysis (H 3 O + or H + /H 2 O) Basic Hydrolysis (OH - /H 2 O) Problems 15.1 to 15.41
17 Chemistry 506 Dr. Hunter s Class Chapter F Section(s) 18.2 Amino Acids having Amide Containing Side Chains Amino Acids (Building Blocks of Proteins) Generic AA = H 2 N-CHR-CO 2 H Asparagine (neutral polar) R = CH 2 C(=O)-NH 2 Glutamine (neutral polar) R = CH 2 CH 2 C(=O)-NH 2
18 Chemistry 506 Dr. Hunter s Class Chapter Index of Topics and Vocabulary 1 1,3-C 4 H 4 N A Acid Chlorides... 15, 16 Acid/Base Chemistry Acidic Acidic Hydrolysis Alkyl Amines... 4 Alkyl Halides Amide Reactions Amides Amine Basicity Amine Classification... 2 Amines... 2, 15, 16 Amino Acids... 9, 18 Amino Acids having Amide Containing Side Chains Amino Acids having Amine/Heterocyclic Containing Side Chains... 9 Ammonia... 2 ammonium salts anamide Anhydrides Aniline... 5 Arginine... 9 aromatic... 9 Aromatic Amines... 5 Asparagine B Basic Basic Hydrolysis Benzamide Bp... 7, 13 Butanamide C C 4 H 5 N... 6 C 4 H 9 N... 6 C 5 H 11 N... 6 C 5 H 5 N... 6 Cadaverine... 7 Carboxylic Acids... 15, 16 coal tar... 5, 6 D Deprotonatio deprotonation Dimethyl Amine... 4 Direct Synthesis G Glutamine H H + /H 2 O H 3 O H-Bonding acceptors... 7 H-bonding donors... 7 Heterocyclic Amines... 6 Histidine... 9 Hydrogen Bonding... 7, 13 Hydrogen Bonding Acceptor... 7 Hydrogen Bonding Donor... 7 Hydrolysis I IUPAC... 4, 14 L Lone Pairs Lysine... 9 M Methyl Ethyl Amine... 4 Mp... 7, 13 N N,N-dimethylbutanamide Neutralization NH 2 R NH NHR N-methyl-N-ethyl aniline... 5 Nomenclature... 4, 14 NR Nucleophilic Attack Nylon O OH OH - /H 2 O P Piperidine... 6 Polar... 7 Polarization of Bonds Polyamides Primary Amine... 2
19 Chemistry 506 Dr. Hunter s Class Chapter Problems Properties... 7, 13 Protein Backbones Proteins... 9, 18 Putrescine... 7 Pyridine... 6 Pyrimidine... 6 Pyrole... 6 Pyrrolidine... 6 Q Quaternary Ammonium Salts... 3 S Secondary Amine... 2 Solubility... 7 Stench!... 7 T Tertiary Amine... 3 Tetramethyl Ammonium Chloride... 4 Thermolysis Tryptophan... 9
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